X-Gluc

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Structural formula
Structural formula of X-Gluc
General
Surname X-Gluc
other names
  • Cyclohexylammonium salt of 5-bromo-4-chloro-3-indolyl-β- D -glucuronic acid
  • Cyclohexylammonium salt of (2 S , 3 S , 4 S , 5 R ) -6 - [(5-bromo-4-chloro-1 H -indol-3-yl) oxy] -3,4,5-trihydroxyoxane-2- carboxylic acid
Molecular formula C 14 H 13 BrClNO 7
Brief description

whitish powder

External identifiers / databases
CAS number 114162-64-0
EC number 601-302-0
ECHA InfoCard 100.132.050
PubChem 152244
Wikidata Q1675010
properties
Molar mass 422.61 g mol −1
Physical state

firmly

solubility

slightly soluble in water

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

X-Gluc stands for the cyclohexylammonium salt of 5-bromo-4-chloro-3-indolyl-β- D -glucuronic acid. X-Gluc is a glycoside and artificial substrate for the enzyme β-glucuronidase (GUS).

properties

The enzyme β-glucuronidase hydrolyzes X-Gluc to glucuronic acid and 5-bromo-4- chloroindoxyl . The 5-bromo-4-chloro-indoxyl is oxidized by the oxygen in the air to the deep blue dye 5,5'-dibromo-4,4'-dichloro- indigo .

Enzymatic cleavage of the X-Gluc leads to the formation of 5-bromo-4-chloro-indoxyl ( 1 ). After oxidation in air and dimerization, this forms the blue dye 5,5'-dibromo-4,4'-dichloro-indigo ( 2 ).

use

The X-Gluc measurement is a simple optical method for checking the β-glucuronidase activity in living cells .

This method with Gus as the reporter gene can be used, for example, in plant transformations to test the transformation efficiency and, in contrast to the MUG assay, is a non-invasive method for GUS detection.

In addition, by combining the β-glucuronidase gene with the promoter of any gene, its expression can be examined in a tissue-specific manner. In contrast to the MUG assay, in which the expression can be measured quantitatively via the activity of the enzyme , the expression of a gene is qualitatively measured indirectly via the activity of the promoter.

Individual evidence

  1. ↑ a b c d Data sheet X-Gluc (PDF) from Carl Roth , accessed on May 8, 2011.

See also